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Synthetic method of fexofenadine intermediate

A fexofenadine and synthetic method technology, applied in the field of organic synthesis route design and preparation of pharmaceutical intermediates, can solve the problems of condensation influence, difficult separation of impurities, low purity, etc., and achieve the effect of low cost and high yield

Active Publication Date: 2017-02-08
ABA CHEM SHANGHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it is hydrolyzed into ester using a one-pot method, which makes it difficult to separate the impurities produced, which has a great impact on the subsequent condensation, resulting in low purity.

Method used

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  • Synthetic method of fexofenadine intermediate

Examples

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Embodiment 1

[0033] Example 1: In a 1000mL reaction flask, add 50g of phenylacetonitrile, 140g of potassium hydroxide and 250mL of dimethyl sulfoxide, stir at room temperature for 1 hour, add 132g of dimethyl sulfate dropwise, and control the temperature at 35-40°C. React for 1 hour under HPLC monitoring; after the reaction is complete, pour the reaction solution into 1000 g of a stirred ice-water mixture, extract 200 mL*2 with dichloromethane, combine the organic phases, wash with water and saturated brine successively, dry over anhydrous sodium sulfate, and concentrate Obtain a red liquid; put the obtained red liquid into a reaction flask, add 250ml of water and 85g of sodium hydroxide in sequence, heat up and reflux for 48h, monitor by HPLC, after the reaction is complete, cool to 20-25°C, and dichloromethane 100mL*2 Extract the impurities, discard them, acidify the aqueous layer with concentrated hydrochloric acid to pH 1-2, and precipitate a large amount of solids, filter, wash with wa...

Embodiment 2

[0034] Example 2: In a 1000mL reaction flask, add 50g of phenylacetonitrile, 102.4g of sodium hydroxide and 250mL of dimethyl sulfoxide, stir at room temperature for 1 hour, add 118.3g of dimethyl sulfate dropwise, and control the temperature at 35-40°C. React at this temperature for 1 hour, and monitor by HPLC; after the reaction is complete, pour the reaction solution into 1000 g of stirred ice-water mixture, extract 200 mL*2 with dichloromethane, combine the organic phases, wash with water and saturated brine in sequence, and dry over anhydrous sodium sulfate , concentrated to obtain a red liquid; put the obtained red liquid into a reaction flask, add 250ml of water and 85g of sodium hydroxide in turn, heat up and reflux for 48h, monitor by HPLC, after the reaction is complete, cool to 20-25°C, and dichloromethane 100mL *2 extract impurities, discard them, acidify the aqueous layer with concentrated hydrochloric acid to pH 1-2, precipitate a large amount of solids, filter, w...

Embodiment 3

[0035]Example 3: In a 1000mL reaction flask, add 50g of phenylacetonitrile, 95.8g of potassium hydroxide and 250mL of dimethyl sulfoxide, stir at room temperature for 1h, add 161.5g of dimethyl sulfate dropwise, control the temperature at 35-40°C, complete the addition, and React at this temperature for 1 hour, and monitor by HPLC; after the reaction is complete, pour the reaction solution into 1000 g of stirred ice-water mixture, extract 200 mL*2 with dichloromethane, combine the organic phases, wash with water and saturated brine in sequence, and dry over anhydrous sodium sulfate , concentrated to obtain a red liquid; put the obtained red liquid into a reaction flask, add 250ml of water and 85g of sodium hydroxide in turn, heat up and reflux for 48h, monitor by HPLC, after the reaction is complete, cool to 20-25°C, and dichloromethane 100mL *2 extract impurities, discard them, acidify the aqueous layer with concentrated hydrochloric acid to pH 1-2, precipitate a large amount ...

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Abstract

The invention provides a synthetic method of a fexofenadine intermediate 2-[4-[4-[4-(hydroxybenzhydryl)-1-piperidyl]-butyryl]phenyl]-2- methylmethacrylate. The method comprises the following steps: methylation of phenylacetonitrile which is used as a raw material, basic hydrolysis, weinreb amidation reaction, Friedel-crafts reaction, acid hydrolysis, esterification and condensation. The method has the following advantages: raw materials and auxiliary materials are cheap and easily available; yield is high; cost is low; there is no meta-isomer; and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis route design and preparation of pharmaceutical intermediates, in particular to a fexofenadine intermediate 2-[4-[4-[4-(hydroxybenzhydryl)-1-piperidine Base]-butyryl]phenyl]-2-methyl propionate synthetic method. Background technique [0002] The chemical name of fexofenadine is 2-[4-[1-hydroxy-4-[4-(hydroxybenzhydryl)-1-piperidinyl]butyl]phenyl]-2-methylpropionic acid , the molecular formula is C 32 h 39 NO 4 . Clinical use is its racemate hydrochloride. Fexofenadine is a new generation of receptor antagonist without sedation and drowsiness. It was developed by Hermero (HMR) in Germany and was first listed in the United States after being approved by the FDA in 1996. , the product name is Allegra, and then it was launched in the United Kingdom, Sweden, Australia and other countries, and the sales volume in the Chinese market is also increasing. As a safe substitute, fexofenadine mu...

Claims

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Application Information

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IPC IPC(8): C07D211/22
CPCC07D211/22
Inventor 肖方亮周宇张敏康胡治国
Owner ABA CHEM SHANGHAI
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